Phenol → HCID 13102629, compound

HRID 460181Notes

Reaction equation

HRID 460181 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:14][CH2:15][O:16][C:17](C)=[O:18]>>[O:13]([C:2]1[S:3][CH:4]=[C:5]([C:17]([O:16][CH2:15][CH3:14])=[O:18])[N:6]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 8857Ethyl AcetateHCID 764302-Bromothiazole

Product 1

HCID 13102629HCID 13102629, compound

Conditions

Temperature
180 °C

Procedure

A mixture of the bromothiazole (1.03 g, 4.36 mmol) and phenol (10.0 g, 106 mmol) was stirred at 180° C. for 1 h, cooled to RT, diluted with 100 mL of EtOAc, washed with 1N NaOH (40×3), H2O, and brine, then dried over MgSO4, and concentrated in vacuo to yield a light yellow residue. Purification over silica gel (gradient, 5% to 10% EtOAc/hexanes) provided the title compound. MS m/z: 250 (M+H)++.

Workup

  1. temperaturecooled to RT
  2. washwashed with 1N NaOH (40×3), H2O, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto yield a light yellow residue
  6. customPurification over silica gel (gradient, 5% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6b9b952c4a6b4b93b0cbf9b9da50113b
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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